He enlisted at Chase City, Virginia in the U.S. Army during World War I. Earle Gregory received the Medal of Honor for actions as a U.S. Army sergeant during the Meuse-Argonne Offensive in World War I. He is considered to be the first Virginian to receive the medal and often called the Sergeant York of Virginia.
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The state highway is also named Earle Davis Gregory Highway, named for Earle Davis Gregory, a World War I Medal of Honor recipient.